Diisopropylethylamine → Ethyl [4-({(2-methoxyethyl)[2-methyl-4'-(trifluoromethyl)-1,1'-biphenyl-3-yl]amino}methyl)-2-methylphenoxy]acetate

HRID 1269616Notes

Reaction equation

HRID 1269616 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][NH:5][C:6]1[C:7]([CH3:22])=[C:8]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=2)[CH:9]=[CH:10][CH:11]=1.Br[CH2:24][C:25]1[CH:37]=[CH:36][C:28]([O:29][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])=[C:27]([CH3:38])[CH:26]=1.C(N(CC)C(C)C)(C)C>C(#N)C>[CH3:1][O:2][CH2:3][CH2:4][N:5]([CH2:24][C:25]1[CH:37]=[CH:36][C:28]([O:29][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])=[C:27]([CH3:38])[CH:26]=1)[C:6]1[C:7]([CH3:22])=[C:8]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:19])([F:20])[F:21])=[CH:14][CH:13]=2)[CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 18448418N-(2-Methoxyethyl)-2-methyl-4'-(trifluoromethyl)-1,1'-biphenyl-3-amineHCID 58622841Ethyl [4-(bromomethyl)-2-methylphenoxy]acetate

Product 1

HCID 58622893Ethyl [4-({(2-methoxyethyl)[2-methyl-4'-(trifluoromethyl)-1,1'-biphenyl-3-yl]amino}methyl)-2-methylphenoxy]acetateYield 60.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of N-(2-methoxyethyl)-2-methyl-4′-(trifluoromethyl)-1,1′-biphenyl-3-amine (500 mg, 1.62 mmol) in acetonitrile (30 mL) was added ethyl [4-(bromomethyl)-2-methylphenoxy]acetate (488 mg, 1.7 mmol) and N,N-diisopropylethylamine (295 μl, 1.7 mmol). The resultant mixture was heated for 4.5 h at 80° C. On cooling the solvents were removed in vacuo, the residue diluted with water and extracted with CH2Cl2. The organic solution was passed through a hydrophobic frit and the solvent removed in vacuo. Purification by Biotage™ chromatography (silica, 40 g) eluted with 5% EtOAc/cyclohexane afforded the title compound as a colourless oil (503 mg).

Workup

  1. temperatureOn cooling the solvents
  2. customwere removed in vacuo
  3. additionthe residue diluted with water
  4. extractionextracted with CH2Cl2
  5. customthe solvent removed in vacuo
  6. customPurification by Biotage™ chromatography (silica, 40 g)
  7. washeluted with 5% EtOAc/cyclohexane

Sources & evidence

ORD record
ord-8b847c2b6e4b423e9acf0e52eafe1f06
Source dataset
uspto-grants-2007_04
Patent number
US07199239B2

Reaction notes

Loading…